Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
  • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
  • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
  • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring

Definitions

• the invention relates to new N-aryl nitrogen heterocycles, several processes and new intermediates for their preparation and their use as herbicides.
• N-aryl nitrogen heterocycles have herbicidal properties (cf. e.g. EP-A 61 741, EP-A 83 055 or EP-A 200 872).
• radicals (R 1 , R 2 , Het etc.) which are defined in the active compounds of the formula (I) also have the meanings given for the compounds of the formula (I) in the intermediates and precursors for all definition areas. The same applies to the residues that are mentioned several times in preliminary and intermediate products.
• the saturated or unsaturated hydrocarbon chains such as, for example, alkyl, alkoxy, alkylsulfonyl, alkenyl, alkynyl or cycloalkylalkyl, are each straight-chain or branched.
• Halogen generally represents fluorine, chlorine, bromine or iodine. Halogen is preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
• R 1 is preferably fluorine.
• R 2 is preferably hydrogen.
• R 3 preferably represents hydrogen, propargyl, cyanomethyl, cyanoethyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl or methoxyethoxycarbonyl.
• the anhydrides of the formula (II) required as starting materials for carrying out process (a) according to the invention are known or are obtainable in analogy to known processes (cf., for example, Gazz. Chim. Ital. 57, 300-311 [1927]; DE-OS 3 644 222; J. Org. Chem. 51, 4150-4158 [1986]; Tetrahedron Lett. 25, 6027-6030 [1984]; J. Org. Chem. 42, 4162-4164 [1977]; Liebigs Ann. Chem. 1977, 772-790; Tetrahedron 25, 4099-4108 [1969]; JP 43/9046).
• aminobenzoxazinones of the formula (III) which are furthermore required as starting materials for carrying out process (a) according to the invention are not yet known and are also an object of the invention.
• the benzoxazinones of the formula (XX) thus obtained are then nitrated in a customary manner with nitric acid in sulfuric acid and then likewise reduced in a generally customary manner with a reactant such as iron in acetic acid.
• the carboxylic acid esters of the formula (IV) required as starting materials for carrying out process (b) are generally known compounds of organic chemistry or can be obtained analogously to known processes (cf., for example, US Pat. No. 4,730,006. Pestic. Sci. 16, 277-286 [ 1985]; Chem. Pharm. Bull. 32, 3934-3944 [1984]; Liebigs Ann. Chem. 1983, 1133-1151; Synthesis 1981, 915-917; Tetrahedron Lett. 22, 2485-2486 [1981]; Chem. Ber. 111, 1058-1076 [1978]; Angew. Chem. 89, 344-345 [1977]; Chem. Ber. 110, 942-947 [1977]; Chem.
• the compounds of the formula (Vla) or (VIb) required as starting materials for carrying out process (c) are generally known compounds and can be prepared by processes known per se (cf. Chem. Ber. 105 (1972), 137-149; J. Am. Chem. Soc. 74 (1952), 6305-6406; loc. Cit. 75 (1953), 5400-5402; DE-OS 1 957 312).
• R 9-1 and R 10-1 independently of one another preferably represent hydrogen, Ci-C 6 -alkyl or halogen-Ci-C 4 -alkyl, in particular hydrogen, methyl, ethyl, n- or iso Propyl, n-, iso-, sec- or tert-butyl or halomethyl with 1 to 3 identical or different halogen atoms or R 9-1 and R 10-1 together represent a doubly linked alkanediyl radical with preferably 2 to 6 carbon atoms, in particular for a 1,3-propanediyl radical, a 1,4-butanediyl radical or a 1,5-pentanediyl radical.
• the phenylhydrazines of the formula (VII) are obtained if aminobenzoxazinones of the formula (III) first diazotized in the usual manner with sodium nitrite in the presence of an acid such as, for example, hydrochloric acid and then likewise reduced in a generally customary manner with a reducing agent such as, for example, tin (II) chloride.
• the 1,3-diketones of the formula (VIII) and derivatives of these diketones, such as, for example, enol ethers, enol esters, ketals, enol ether ketals, enamines or ⁇ -halo vinyl ketones, which are further required as starting materials for carrying out process (d), are generally known compounds of organic chemistry.
• R 11-1 preferably represents hydrogen, C 1 -C 6 -alkyl or halogen-Ci-C4-alkyl, in particular hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso -, sec- or tert-butyl or halomethyl with 1 to 3 identical or different halogen atoms, especially fluorine or chlorine.
• N-aryl nitrogen heterocycles of the formula (If) required as starting materials for carrying out process (e) are compounds according to the invention and can be obtained with the aid of processes (d) and (I) according to the invention.
• N-arylpyrazolinones of the formula (IX) required as starting materials for carrying out process (f) according to the invention are not yet known and are also an object of the present invention.
• ⁇ -keto esters of the formula (XXI) are generally known compounds of organic chemistry.
• the phenylhydrazides of the formula (X) required as starting materials for carrying out the process (g) are not yet known and are also an object of the present invention.
• Acylating agents of the formula (XXII) are generally known compounds of organic chemistry.
• the iminocarboxylic esters of the formula (XI) required as starting materials for carrying out process (h) are known or are obtainable in analogy to known processes (cf., for example, Chem. Ber. 119, 2444-2457 [1986]; Bull. Chem. Soc. Jpn 55, 3943-3944 [1982]; Chem. Lett. 1982, 1015-1016; Chem. Lett. 1978, 1403- 1404; J. Amer. Chem. Soc. 95, 3957-3963 [1973]; J. Org. Chem. 36, 3251-3252 [1971]).
• R 18th and R 19 independently of each other v or preferably for C 1 -C 4 alkyl, especially for methyl or ethyl.
• N-aryl nitrogen heterocycles of the formula (Ii) required as starting materials for carrying out process (i) are compounds according to the invention and can be obtained using process (h) according to the invention.
• alkylating agents of the formula (XII) which are also required as starting materials are generally known compounds of organic chemistry.
• R 14-1 is preferably C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkynyl, halo-Ci-C 4 - alkyl having 1 to 9 identical or different halogen atoms, halogen-C 3 -C 6 -alkenyl with 1 to 5 identical or different halogen atoms or halogen-C 3 -C 6 -alkynyl with 1 to 5 identical or different halogen atoms.
• R 14-1 stands in particular for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for methyl, ethyl or t substituted in each case once, twice or three times by fluorine and / or chlorine -Butyl, for allyl, n- or i-butenyl, chlorallyl, dichlorallyl, propargyl or chloropropyl.
• E 1 preferably represents halogen, in particular chlorine, bromine or iodine, or optionally substituted alkylsulfonyloxy, alkoxysulfonyloxy or arylsulfonyloxy, such as methanesulfonyloxy, trifluoromethanesulfonyloxy, methoxysulfonyloxy, ethoxysulfonyloxy or p-toluenesulfonyloxy.
• halogen in particular chlorine, bromine or iodine
• optionally substituted alkylsulfonyloxy, alkoxysulfonyloxy or arylsulfonyloxy such as methanesulfonyloxy, trifluoromethanesulfonyloxy, methoxysulfonyloxy, ethoxysulfonyloxy or p-toluenesulfonyloxy.
• amidrazones of the formula (XIII) required as starting materials for carrying out process (j) according to the invention are not yet known.
• R 13-1 and R 14-2 preferably together represent a double-linked alkanediyl radical having 2 to 6 carbon atoms, in particular a 1,3-propanediyl radical, a 1,4-butanediyl radical or a 1,5-pentanediyl radical.
• amidrazones of the formula (XIII) are obtained in analogy to known processes (cf., for example, US Pat. No. 4,080,192 or DE-OS 1,957,783) if lactams of the formula (XXIII) first in a first stage with a halogenating agent such as phosphorus oxychloride, thionyl chloride or phosgene if appropriate in the presence of a diluent such as ethanol or dioxane and optionally in the presence of a reaction auxiliary such as triethylamine or pyridine at temperatures between 0 ° C and 50 ° C and then the imide chlorides of the formula (XXIV) obtainable in this way, with phenylhydrazines of the formula (VII), optionally in the presence of a diluent such as ethanol and optionally in the presence of a reaction auxiliary such as triethylamine or pyridine at temperatures between 0 ° C and 80 ° C.
• Lactams of the formula (XXIII) are generally known compounds of organic chemistry.
• the hydroxyisobenzfuranone of the formula (XIV) required as a starting material for carrying out process (k) according to the invention is a generally known compound of organic chemistry.
• N-aryl nitrogen heterocycles required as starting materials for carrying out process (I) of the formula (In) are compounds according to the invention and can be obtained with the aid of processes (a) to (k) according to the invention.
• the further alkylation or acylating agents of the formula (XVI) are known compounds of organic chemistry.
• E2 preferably stands for halogen, in particular for chlorine, bromine or iodine, or for optionally substituted alkylsulfonyloxy with preferably 1 to 4 carbon atoms, alkoxysulfonyloxy with preferably 1 to 4 carbon atoms or arylsulfonyloxy with preferably 6 to 10 carbon atoms, such as in particular methanesulfonyloxy, trifluoromethanesulfonyloxy, methoxysulfonyloxy , Ethoxysulfonyloxy or p-toluenesulfonyloxy.
• Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
• diluents for carrying out process (a) according to the invention.
• These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether, Ketones, such as acetone or butanone, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl
• process (a) according to the invention can be carried out in the presence of a suitable reaction auxiliary.
• Inorganic or organic acids such as acetic acid or p-toluenesulfonic acid, anhydrides such as acetic anhydride or acid chlorides such as acetyl chloride are preferably used as reaction aids.
• other customary water-releasing agents such as, for example, N, N'-dicyclohexylcarbodiimide, or customary acylation catalysts, such as, for example, 4- (N, N-dimethylamino) pyridine as reaction aids.
• reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 20 ° C and 180 C, preferably at temperatures between 50 ° C and 150 ° C.
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol - or -diethyl ether, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide or alcohols such as methanol, ethanol or propanol.
• Process (b) according to the invention is optionally carried out in the presence of a suitable reaction auxiliary.
• All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, and also tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO) or diazabicyclone (DABCO), diazabicyclone Diazabicycloundecene (DBU).
• alkali metal hydroxides such as sodium hydroxide or potassium hydroxide
• alkali metal carbonates such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate
• tertiary amines such as triethylamine, N, N-dimethylaniline, pyr
• reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and 150 C, preferably at temperatures between 20 ° C and 120 ° C.
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Suitable diluents are preferably high-boiling, inert organic solvents. These include above all, optionally halogenated, hydrocarbons, such as decalin, Tetralin, toluene, xylene, also chlorobenzene and 1,2-dichlorobenzene and mesitylene.
• reaction temperatures can be varied within a substantial range in process (c) according to the invention. In general, temperatures between 80 ° C and 250 ° C, preferably at temperatures between 120 ° C and 220 ° C.
• Process (c) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• process (c) the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
• the reactions are generally carried out in a suitable diluent, but if appropriate also without a diluent, and the reaction mixture is stirred at the temperature required in each case.
• Working up in process (c) according to the invention is carried out in each case by customary methods.
• Inert organic solvents are suitable as diluents for carrying out processes (d) and (k) according to the invention.
• These include in particular aliphatic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, nitrate Acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide, esters such as ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as
• Processes (d) and (k) according to the invention are optionally carried out in the presence of a suitable reaction auxiliary.
• a suitable reaction auxiliary inorganic mineral acids such as hydrochloric acid or sulfuric acid are suitable as such.
• inorganic mineral acids such as hydrochloric acid or sulfuric acid are suitable as such.
• phenylhydrazines of the formula (VII) which are suitable as starting materials in the form of corresponding acid addition salts, such as, for example, hydrochlorides.
• reaction temperatures can be varied within a substantial range when carrying out processes (d) and (k) according to the invention. In general, temperatures between -20 ° C and 180 C, preferably at temperatures between 20 ° C and 120 ° C.
• the desired reaction products of the formula (Id) can be isolated from these isomer mixtures using customary separation processes (distillation, crystallization, chromatography).
• Suitable halogenating agents for carrying out process (e) according to the invention are customary halogenating agents.
• Sulfuryl chloride, elemental chlorine or elemental bromine are particularly preferably used as halogenating agents.
• Inert organic solvents are suitable as diluents for carrying out process (e) according to the invention.
• diluents for carrying out process (e) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, 0-dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride.
• reaction temperatures can be varied within a substantial range when carrying out process (e) according to the invention. In general, temperatures between 0 ° C and 150 C, preferably at temperatures between 35 ° C and 70 C.
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Suitable halogenating agents for carrying out process (f) according to the invention are also conventional halogenating agents.
• inorganic acid halides such as phosphorus oxychloride, thionyl chloride, phosgene, phosphorus tribromide or diphosgene (Cl 3 CO-CO-Cl) are used.
• Inert organic solvents are suitable as diluents for carrying out process (f) according to the invention.
• diluents for carrying out process (f) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, O-dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride or basic diluents such as pyridine. It is also possible to use an appropriate excess of halogenating agent at the same time as a diluent.
• Process (f) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
• Suitable auxiliary nucleophiles such as triphenylphosphine, dimethylaniline or dimethylformamide are particularly suitable as such.
• reaction temperatures can be varied within a substantial range when carrying out process (f) according to the invention. In general, temperatures between 0 ° C and 200 C, preferably at temperatures between 30 ° C and 150 C.
• reaction auxiliaries 1 to 10 mol, preferably 1 to 5 mol of halogenating agent and optionally 0.01 to 1 mol, preferably 0.05 to 0.1 mol, of reaction auxiliaries are generally employed per mol of N-arylpyrazolinone of the formula (IX) .
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out processes (g) and (j) according to the invention.
• These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, 0-dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride.
• Processes (g) and (j) according to the invention are preferably carried out in the presence of a suitable reaction auxiliary.
• a suitable reaction auxiliary As such, all common bases come into question. Particular preference is given to using tertiary amines such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
• reaction temperatures can be varied within a substantial range when carrying out processes (g) and (j) according to the invention. In general, temperatures between -20 ° C and 180 ° C, preferably at temperatures between 0 ° C and 150 ° C.
• reaction auxiliaries 1 to 5 mol, preferably 1 to 1.5 mol of phosgene and optionally 1 to 5 mol, preferably 1 to 3 mol, of reaction auxiliaries are generally employed per mol of amidrazone of the formula (XIII) .
• reaction is carried out, worked up and isolated according to generally customary methods.
• reaction auxiliaries are generally employed per mol of phenylhydrazide of the formula (X) .
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out process (h) according to the invention.
• These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether, Ketones such as acetone or butanone, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, esters such as ethyl acetate, sulfoxides
• reaction temperatures can be varied within a substantial range when carrying out process (h) according to the invention. In general, temperatures between 0 ° C and 180 C, preferably at temperatures between 50 ° C and 150 C.
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out process (i) according to the invention.
• Aliphatic, cyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene or dichlorobenzene, ethers, such as diethyl ether, are preferably used.
• Alkali metal hydrides, hydroxides, amides, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium hydroxide, sodium carbonate, potassium carbonate or sodium hydrogen carbonate, or else tertiary amines, such as, for example, triethylamine, N, N-dimethylaniline, pyridine, 4-, are preferably used.
• N, N-Dimethylamino pyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
• reaction temperatures can be varied within a substantial range when carrying out the production process (i). Generally one works between -20 C and +150 C, preferably between 0 ° C and +100 C.
• reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
• Inert organic solvents are suitable as diluents for carrying out process (I) according to the invention.
• Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene or dichlorobenzene, ethers, such as diethyl ether, are preferably used.
• Alkali metal hydrides, hydroxides, amides, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium hydroxide, sodium carbonate or sodium hydrogen carbonate, or else tertiary amines, such as, for example, triethylamine, N, N-dimethylaniline, pyridine, 4- (N , N-dimethylamino) pyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
• DABCO diazabicyclooctane
• DBN diazabicyclonones
• DBU diazabicycloundecene
• reaction temperatures can be varied within a substantial range when carrying out process (I) according to the invention. Generally one works between -20 C and + 150 ° C, preferably between 0 ° C and +100 ° C.
• the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the active compounds according to the invention can e.g. used in the following plants: dicot weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirs Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.
• the compounds are suitable for total weed control, e.g. on industrial and track systems and on waves and squares with and without tree cover.
• the weed control compounds in permanent crops, e.g. Forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
• the active compounds of the formula (I) according to the invention are particularly suitable for the selective weed control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops in the pre- and post-emergence process.
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances, and very fine encapsulations in polymeric substances.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can also be used as auxiliary solvents.
• auxiliary solvents e.g. organic solvents
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used in a mixture with known herbicides for weed control, finished formulations or tank mixes being possible.
• herbicides such as e.g.
• Aryloxalkanoic acids such as 2.4 D, 2.4 DP, 2.4 DB, MCPA, MCPP, fluroxypyr;
• Aryloxy-phenoxy-alkanoic acid esters such as diclofop-methyl, fenoxaprop, fluazifop-butyl, quizalofop, haloxyfop;
• Aryl carboxylic acids such as clopyralide;
• Azinones such as chloridazon, norflurazon; Carbamates such as phenmedipham; Chloroacetanilides such as alachlor, metazachlor, metolachlor; Dinitroanilines such as oryzalin, pendimethalin, trifluralin;
• Diphenyl ethers such as acifluorfen, bifenox, fomesafen, lactofen, oxyfluorfen;
• Ureas such as chlorotoluron, flurmeturon, isoproturon
• a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
• the active compounds according to the invention can be applied both before and after emergence of the plants.
• the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 0.001 and 10 kg of active ingredient per hectare of soil, preferably between 0.005 and 5 kg per ha.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
• Test plants which have a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
• the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
• Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

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• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
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• Plural Heterocyclic Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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• 1989
  • 1989-11-04 DE DE3936826A patent/DE3936826A1/de not_active Withdrawn
• 1990
  • 1990-09-28 US US07/590,418 patent/US5108483A/en not_active Expired - Fee Related
  • 1990-10-20 EP EP19900120149 patent/EP0427031A3/de not_active Withdrawn
  • 1990-10-30 JP JP2290963A patent/JPH03153685A/ja active Pending

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